Waylon Jennings and Jessi Colter
Waylon Jennings and Jessi Colter shared a love of music and an independent streak. Jennings’ first flirtation with music was as a disc jockey at the ripe age of 14. By 18 he was playing bass with his childhood friend Buddy Holly. Colter spent much of her sheltered and solitary childhood under her mother's watchful eye, writing songs and playing the piano in church. Her passion for country music ignited when she first heard the notorious George Jones. At the age of 14 she produced her first single, “Lonesome Road.”
They met in the 1960s and their initial connection, according to Colter, was intense. They married in 1969. Along with his friends Johnny Cash and Willie Nelson, Jennings was part of a movement in country music that broke from previously established norms. Collaboration wasn't encouraged within the industry, but Jennings didn’t care: In 1976 he cut the album Wanted: The Outlaws with Colter, Willie Nelson, and Tompall Glaser. It became the first platinum album ever recorded in Nashville.
Teaming up in the ‘80s with Willie Nelson, Kris Kristofferson and Johnny Cash, Jennings formed the country supergroup The Highwaymen. As his career soared, Jennings struggled with drug addiction, which Colter tried to help him overcome. Jennings died of complications from diabetes in 2002. Colter still plays music today.